Enantioselective Cationic Polyene Cyclization vs Enantioselective Intramolecular Carbonyl-Ene Reaction

Journal of the American Chemical Society

Volumn 132, Issue 30, 2010, Pages 10242-10244

  Zhao, Yu Jun ^a,b   Li, Bin ^a   Tan, Li Jun Serena ^a   Shen, Zhi Liang ^a   Loh, Teck Peng ^a  

^a Nanyang Technological University   (Singapore)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUILDING BLOCKES; CARBONYL-ENE REACTIONS; CYCLIZATION PRODUCTS; ENANTIOSELECTIVE; ENANTIOSELECTIVE REACTIONS; HIGH ENANTIOSELECTIVITY; HIGH YIELD; MECHANISTIC DIFFERENCES; NATURAL PRODUCTS;

CARBONYLATION; ENANTIOSELECTIVITY; ORGANIC COMPOUNDS;

CYCLIZATION;

CARBONYL DERIVATIVE; NATURAL PRODUCT; POLYENE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; CYCLIZATION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 77955030465     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja104119j     Document Type: Article

References (48)

1. Yoder, R. A. and Johnston, J. N. Chem. Rev. 2005, 105, 4730-4756
2. Johnson, W. S. Tetrahedron 1991, 47, xi-1
3. Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 341.
4. For reviews: Oppolzer, W. and Snieckus, V. Angew. Chem., Int. Ed. 1978, 17, 476-486
5. Clarke, M. L. and France, M. B. Tetrahedron 2008, 64, 9003-9031
6. Mikami, K., Terada, M., Narisawa, S., and Nakai, T. Synlett 1995, 255-265
7. Mikami, K. and Shimizu, M. Chem. Rev. 1992, 92, 1021-1050 For recent progress: Evans, D. A. and Wu, J. J. Am. Chem. Soc. 2005, 127, 8006-8007
8. Evans, D. A. and Aye, Y. J. Am. Chem. Soc. 2006, 128, 11034-11035
9. Mikami, K., Terada, M., and Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954
10. Mikami, K. and Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039-7040
11. Zheng, K., Shi, J., Liu, X., and Feng, X. J. Am. Chem. Soc. 2008, 130, 15770-15771
12. Zhao, J. F., Tsui, H. Y., Wu, P. J., Lu, J., and Loh, T. P. J. Am. Chem. Soc. 2008, 130, 16492-16493
13. Sakakura, A., Ukai, A., and Ishihara, K. Nature 2007, 445, 900-903
14. Rendler, S. and MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 5027-5029
15. Knowles, R. R., Lin, S., and Jacobsen, E. N. J. Am. Chem. Soc. 2010, 132, 5030-5032
16. Yang, D., Gu, S., Yan, Y.-L., Zhao, H.-W., and Zhu, N. Y. Angew. Chem., Int. Ed. 2002, 41, 3014-3017
17. Yamamoto, H., Ishihara, K., and Ishibashi, H. J. Am. Chem. Soc. 2004, 126, 11122-11123 and references therein
18. Mullen, C. A., Campbell, M. A., and Gagné, M. R. Angew. Chem., Int. Ed. 2008, 47, 6011
19. Surendra, K. and Corey, E. J. J. Am. Chem. Soc. 2009, 131, 13928-13929
20. Topczewski, J. J., Callahan, M. P., Neighbors, J. D., and Wiemer, D. F. J. Am. Chem. Soc. 2009, 131, 14630-14631
21. Yang, D., Yang, M., and Zhu, N. Y. Org. Lett. 2003, 5, 3749-3752
22. Grachan, M. L., Tudge, M. T., and Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, 1469-1472 and references therein
23. Sakane, S., Maruoka, K., and Yamamoto, H. Tetrahedron Lett. 1985, 26, 5535-5538
24. Kaden, S. and Hiersemann, M. Synlett 2002, 1999-2002
25. Abouabdellah, A. and Bonnet-Delpon, D. Tetrahedron 1994, 50, 11921-11932
26. Zhao, Y. J. and Loh, T. P. Org. Lett. 2008, 10, 2143-2145
27. Zhao, Y. J., Tan, L. J. S., Li, B., and Loh, T. P. Chem. Commun. 2009, 3738-3740
28. Zhao, Y. J. and Loh, T. P. J. Am. Chem. Soc. 2008, 130, 10024-10029
29. Zhao, Y. J., Chng, S. S., and Loh, T. P. J. Am. Chem. Soc. 2007, 129, 492-493
30. van Tamelen, E. E. and Leiden, T. M. J. Am. Chem. Soc. 1982, 104, 1785-1786
31. Fish, P. V. and Johnson, W. S. J. Org. Chem. 1994, 59, 2324-2335
32. Uyanik, M., Ishihara, K., and Yamamoto, H. Org. Lett. 2006, 8, 5649-5652
33. Aggarwal, V. K., Vennall, G. P., Davey, P. N., and Newman, C. Tetrahedron Lett. 1998, 39, 1997-2000
34. Hanhan, N. V., Sahin, A. H., Chang, T. W., Fettinger, J. C., and Franz, A. K. Angew. Chem., Int. Ed. 2010, 49, 744-747
35. Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, p 341.
36. Sutherland, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 1.9, p 341.
37. Yang, D., Ye, X. Y., Gu, S., and Xu, M. J. Am. Chem. Soc. 1999, 121, 5579-5580
38. Yang, D., Xu, M., and Bian, M. Y. Org. Lett. 2001, 3, 111-114
39. Garver, L. C. and van Tamelen, E. E. J. Am. Chem. Soc. 1982, 104, 867-869
40. van Tamelen, E. E. and Leiden, T. M. J. Am. Chem. Soc. 1999, 104, 1785-1786
41. Johannsen, M. and Jørgensen, K. A. J. Org. Chem. 1995, 60, 5757-5762
42. Evans, D. A., Johnson, J. S., Burgey, C. S., and Campos, K. R. Tetrahedron Lett. 1999, 40, 2879-2882
43. Thorhauge, J., Roberson, M., Hazell, R. G., and Jørgensen, K. A. Chem.=Eur. J. 2002, 8, 1888-1898
44. Lu, J., Hong, M. L., Ji, S. J., and Loh, T. P. Chem. Commun. 2005, 1010-1012
45. Stork, G. and Burgstahler, A. W. J. Am. Chem. Soc. 1955, 77, 5068-5077
46. Eschenmoser, A., Ruzika, L., Jeger, O., and Arigoni, D. Helv. Chim. Acta 1955, 38, 1890-1904
47. Eschenmoser, A. and Arigoni, D. Helv. Chim. Acta 2005, 88, 3011-3050
48. Staschke, K. A., Hatch, S. D., Tang, J. C., Hornback, W. J., Munroe, J. E., Colacino, J. M., and Muesing, M. A. Virology 1998, 248, 264-274